Mehta, G. ; Venkatesan, K. ; Moorthy, J. N. ; Begum, N. S. ; Padma, S. (1992) Synthetic studies towards prismanes - rearrangements in some pentacyclic precursors and X-ray crystal-structure of a novel heptacyclic ether Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 31 (8). pp. 473-482. ISSN 0376-4699
Full text not available from this repository.
Official URL: http://www.niscair.res.in/ScienceCommunication/Res...
Abstract
In order to gain access to the heptacyclic tetraone 3, efforts were directed towards the utilisation of the major 'unwanted' [4 + 2]-adduct 11 of tetrachlorodimethoxycyclopentadiene and norbornenobenzoquinone. Epoxides derived from the diol and dimethoxy derivatives of the adduct 11 undergo facile Wagner-Meerwein rearrangement resulting in the required endo, syn, endo stereochemistry as well as methano-bridge functionalisation to deliver 18 and 24, respectively. However, intramolecular ether formation, occurring via the capture of carbocation intermediate with the transannularly poised oxygen functionality, is a more facile process. Attempts to cleave the ether linkage resulted in the formation of a novel transannularly cyclised twisted bowl shape heptacyclic compound 30 and its structure has been established through X-ray crystallography.
Item Type: | Article |
---|---|
Source: | Copyright of this article belongs to National Institute of Science Communication and Information Resources. |
ID Code: | 81868 |
Deposited On: | 08 Feb 2012 12:37 |
Last Modified: | 16 Jul 2012 15:30 |
Repository Staff Only: item control page